Thionyl Chloride → 4-Amino-1-benzylpiperidine-4-carboxylic acid hydrochloride

HRID 251459Notes

Reaction equation

[NH2:1][C:2]1([C:15]([OH:17])=[O:16])[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.S(Cl)([Cl:20])=O>CO>[ClH:20].[NH2:1][C:2]1([C:15]([OH:17])=[O:16])[CH2:3][CH2:4][N:5]([CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:6][CH2:7]1

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of 4-amino-1-benzylpiperidine-4-carboxylic acid (5 g, 21 mmol) in methanol (90 ml) is cooled down to 0° C. and treated dropwise with thionyl chloride. The mixture is then brought to reflux for 5 hours and stirred at 20° C. overnight. The mixture is concentrated under reduced pressure, the residue is taken up in toluene and concentrated again to give 6.14 g of 4-amino-1-benzylpiperidine-4-carboxylic acid hydrochloride ax58 as a hygroscopic white solid.

Workup

temperatureto reflux for 5 hours
concentrationThe mixture is concentrated under reduced pressure
concentrationconcentrated again

Sources & evidence

ORD record: ord-7bc9aeb12d4d4ec189bdce323c8606d6
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863450B2

Reaction notes

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